2-Bromo-1-(4-hydroxyphenyl)ethanone → HCID 13654483, compound

HRID 424433Notes

Reaction equation

HRID 424433 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)=[O:9].C(N(CC)CC)C>O1CCCC1>[CH3:1][S:2]([O:16][C:13]1[CH:14]=[CH:15][C:10]([C:8](=[O:9])[CH2:7][Br:6])=[CH:11][CH:12]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 13654483HCID 13654483, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (50 g, 436 mmol) was added to a solution of 2-bromo-1-(4-hydroxyphenyl)-ethan-1-one (85 g, 395 mmol) and triethylamine (48 g, 474 mmol in tetrahydrofuran (1000 ml) at 0° C. and the mixture was stirred for 30 minutes at room temperature. The mixture was partitioned between water and ethyl acetate, and the organic layer was washed with brine, dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was washed with diisopropyl ether to afford 4-(2-bromoacetyl)phenyl methanesulfonate (96 g, 83%) as white crystals.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-233992de7ba74cfa83d47291c55375eb
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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